Donald Penn – T 2007-2013
The Minnesota Vikings signed Donald Penn as an undrafted free agent out of Utah State in 2006, but he wouldn’t actually see the field until being signed by the Buccaneers the next season in 2007. It ended up being the Buccaneers bargain of the decade.
Penn started in 12 games his first season in Tampa but appeared in all 16. Once he got the starting job, he never relinquished it until he was let go in 2013 in favor of the incomparable Anthony Collins. This mountain of a man in Penn was a stalwart at left tackle, playing in 112 games, and making it to a Pro Bowl in 2010. That offseason, he was rewarded with a six-year, $48 million contract extension.
While the way he exited may not have been the most fitting for a player of Penn’s caliber, getting released then singing with the Raiders where he proceeded to make two Pro Bowls, Penn was, and remains, a fan-favorite. The 315-pound Penn’s reliable play, coupled with his two touchdown catches with the Buccaneers (the second coming in his 100th career game), certainly helped that as well. This was an absolute heist of epic proportions for the Buccaneers, and deserving of a spot on the list.